Preliminary results by the principal investigator indicate that the(3.3)- sigmatropic rearrangement of cyclohexenyl trichloroacetimidates should afford a new and versatile route to compounds possessing 1-azaspiro ring systems. This approach will be developed into a proposed total synthesis of the histrionicotoxin alkaloids and several of their analogs. These novel alkaloids are promising specific probes for neuropharmacological research, and may also hold promise as superior neuromuscular blocking agents as well as exhibiting other cholinergic activities. Specifically, the objectives can be stated as follows: 1) Study the (3.3) -sigmatropic rearrangement of cyclohexenyl trichloroacetimidates as a route to the 1-azaspiro(5.5)undecane ring system. 2) Synthesize, in a stereospecific fashion, perhydrohistrionicotoxin and the natural alkaloid histrionicotoxin. 3) Synthesize several histrionicotoxin analogs and do preliminary testing of their neuromuscular blocking activity.